Potassium Carbonate → HCID 54230499, compound

HRID 1276037Notes

Reaction equation

HRID 1276037 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[CH:17]=[CH:16][C:15]([OH:19])=[CH:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4].C(=O)([O-])[O-].[K+].[K+].[N+:26]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br)([O-:28])=[O:27]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[CH:17]=[CH:16][C:15]([O:19][CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([N+:26]([O-:28])=[O:27])[CH:30]=1)=[CH:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 135618678HCID 135618678, compound

Product 1

HCID 54230499HCID 54230499, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxyacridine-9-carboxylic acid methyl ester (14.6 g; 57.7 mmol) was dissolved in 500 ml DMF, then potassium carbonate (25.0 g; 181 mmol) and m-nitrobenzylbromide (15.0 g; 69.4 mmol) were added and stirred at room temperature. After 4 hours the mixture was filtered and the filtrate was evaporated to dryness in vacuo. The residue was dissolved in CH2Cl2 and washed with HCl 1N, NaOH 1N and sodium chloride solution (10%). After drying with sodium sulfate and evaporating to dryness the residue was flash chromatographed (column: 10 cm diameter) in CH2Cl2 +1% methanol (fractions of 200 ml). Fractions 7-23 were combined, evaporated and the residue was collected on a Buchner funnel and washed with diethylether. Yield 8.7 g (39%), Fp.>250° C. 1H-NMR(CDCl3): 5,35(2H, s, CH2) and 4,22 ppm (3H, s, CH3). MS: M+ =388.

Workup

  1. filtrationAfter 4 hours the mixture was filtered
  2. customthe filtrate was evaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with HCl 1N, NaOH 1N and sodium chloride solution (10%)
  5. dry with materialAfter drying with sodium sulfate
  6. customevaporating to dryness the residue
  7. customchromatographed (column: 10 cm diameter) in CH2Cl2 +1% methanol (fractions of 200 ml)
  8. customevaporated
  9. customthe residue was collected on a Buchner funnel
  10. washwashed with diethylether
  11. custom>250° C

Sources & evidence

ORD record
ord-cc4f2c9f0ca0444f861b5c69ef99209e
Source dataset
uspto-grants-2000_12
Patent number
US06165800

Reaction notes

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